Ch_322a_5.014

Ch_322a_5.014 - Relative Configurations at Stereocenters...

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Relative Configurations at Stereocenters For many years before the development of x-ray crystallography, configurations at stereocenters were assigned relatively . The stereocenter in one chiral compound was related to one in another compound through a stereochemically well-defined chemical transformation . C H CH 3 CH 2 OH C 2 H 5 * (S)-(-)-2-methyl-1-butanol [ ! ] D 25 = -5.756 o + HCl heat C H CH 3 CH 2 Cl C 2 H 5 + H 2 O * (S)-(+)-1-chloro-2-methylbutane [ ! ] D 25 = +1.64 o bond-breaking is remote from stereocenter Because the bonding changes are remote from the stereocenter, the configuration of groups around the stereocenter in the product is the same as in the reactant. This reaction proceeds with retention of configuration .
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Relative Configurations: (D)- and (L)-Glyceraldehyde In the late 19th century, Emil Fischer developed a method for assigning configurations at stereocenters relative to the enantiomers of glyceraldehyde . For the next 50 or 60 years, configurations at stereocenters were labeled relative to the stereocenters in the
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This note was uploaded on 07/22/2009 for the course CHEM 322AL taught by Professor Jung during the Summer '07 term at USC.

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Ch_322a_5.014 - Relative Configurations at Stereocenters...

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